This project is concerned with the total synthesis of the naturally occurring insect anti-feedants ajugarin-I, ajugarin-II, and waburganal. The main approach to the ajugarin compounds is via the construction of the bicyclic ring system using a Diels-Alder cycloaddition reaction. The synthetic plan for waburganal is aimed toward the construction of a tricyclic furano compound with further elaboration of the furan ring into the hydroxy dialdehyde system of the natural product. The project is also aimed at the preparation of structural and stereochemical modifications of the ajugarin compounds for the production of substances to be tested as anti-feeding agents.